I Packed Terribly For My Most Recent Trip, But Here's How I Actually Made It Work

I don't like to brag, but as someone who's on a plane at least every other week, I like to think that I'm pretty good at packing. With lots of trial and error, I've set up a system for myself that allows me to maximize my space and avoid checking a bag. But on my most recent trip — two weeks between Puerto Rico, Orlando, and Tampa — I somehow managed to pack a ton of things I didn't need, but none of the things I actually did, so I quickly had to figure out what to do when you didn't pack well for a trip.

I'm not joking about my packing skills. I once packed for a whole month in just a carry-on, and even had room to spare. But somehow when I was rushing to pack for this last trip, I managed to pack three pairs of jeans, but only one T-shirt. A ton of my clothes were bathing suit cover-ups, and I couldn't wear them on their own. I also somehow forgot my iPad, and packed 15 different bathing suits. (General tip: No one needs that many bathing suits for one trip!)

Lo and behold, I still completely filled up my carry-on luggage with absolutely no room to spare. I'm not ashamed to publicly admit that I truly packed terribly for this trip. Not only was it a huge inconvenience from a logistical standpoint, but I was also concerned about taking pictures. Everyone knows that you can get a ton of #content when you're on the road, and I feared that I'd have to repeat my outfits too many times.

It took some creative finagling, but I powered through the two-week trip without running out of clothes — and without repeating things too many times. Here's exactly how I did it.

I made use of what I had, and wore them in different ways.

Unfortunately, I didn't pack enough tops. I only brought one shirt, and the rest of my clothes were bottoms, swimsuits, and one-piece items, like jumpsuits, overalls, and dresses. Obviously, the dresses and jumpsuits could be worn on their own, but I couldn't wear the overalls or bottoms without a top. So, I made use of what I had.

Some bikini tops (like this one from Urban Outfitters) and bralettes (like my go-to one from Aerie) worked as "crop tops" for my high-waisted pants and overalls. Though that boho look might not have worked on a different trip, Puerto Rico was actually the perfect setting for me to wear outfits like that. I was able to layer my crocheted sweaters over the crop tops, too.

Repeating clothes was a necessity, but I found ways to mix up my outfits to keep every look fresh.

In my everyday life, I love wearing pieces differently to give them new life, especially when I repeat them more than once. One of my favorite tricks is to mess with how I wear a T-shirt. My gray V-neck T-shirt got a lot of wear on this trip. (And honestly, I should probably wash it twice when I get home.) I wore it tucked into a pair of high-waisted jeans one day, underneath my overalls on another day, and then tied up and paired with palazzo pants on yet another day.

I also played around with accessories and styling to make clothes look different. I switched out my sneakers for sandals, put my hair up in a ponytail, or wrapped a fanny pack around my waist, all to make a piece of clothing look a little different than the last time I wore it.

I ended up having to buy some new clothes.

I'm not going to lie and say that I was able to get through the entire trip without buying some clothes. I didn't buy a lot — there was pretty much no room in my suitcase for anything else — but I was a little short on clothes that I could wear for nicer occasions, so I stopped by the Valija boutique in Old San Juan to pick up a couple of things. (The jumpsuit in the picture above was one of the things I bought.)

I learned that it's totally possible to get through a trip with limited supplies.

If you're on the road and find yourself short on supplies, these tips can help you make the most of your clothes. I definitely don't want to pack like this for a trip ever again, but I think it was a great challenge to test my creativity when it comes to my clothes when I travel. Maybe now I can possibly find ways to downsize my packing even more and I'll be able to save space on my trips.